The Diary of Tom Riddle
by BigJellyMonster
Summary: Harry notices that Tom Riddle writes more in his diary than he does spending time with his friends. His unrelenting curiosity about just what it is that Riddle writes in it, is only matched by his desire to teach Tom Riddle how to "live a little".
1. Chapter 1

_For Obsidianpen_

Harry didn't normally pay attention in History of Magic Class, but today they were presenting their end of semester projects. They were supposed to be giving presentations of some historical moment or figure of their choice. However, because they've had to suffer Professor Binn's long and unnaturally boring lectures all year, it has become a game to see who can make the funniest presentation.

So far, they've had a retelling of the final battle between Gellert Grindelwald and Albus Dumbledore, with crudely drawn photos of the professors in bikinis in the background, the history of a goblin named Grug the Wood Grower as if told by Professor Snape, and the history of cats in the wizarding world with photos of cats childishly drawn into famous historical paintings.

At one point in the presentation, someone had gathered a bunch of pet cats in the school and invited them all into the classroom. It was chaos as cats of every breed jumped and climbed on everything they could find. Some tried to play with student's robes, some chased imaginary butterflies, and some just wanted to sunbathe by the window.

Every student was laughing, crying, or falling out of their seat by the end of the presentations. Sometimes all three. It was one of the rare moments where the Gryffindor and Slytherin students got along. Harry was proud to see the two houses laughing together so well, and wished that there were more moments like these throughout the year.

One thing he noticed during the presentations, was that Tom Riddle did not look up from his little black book. While everyone else was enjoying themselves, Tom kept writing in his book and rolled his eyes at the rest of the class if they ever got too loud. For some reason, it irritated Harry.

"What's so important that he can't have fun with the rest of us," Harry complained to his friends.

Hermione followed Harry's gaze and shrugged. "I don't know. Maybe he has more important things to do. Being top of the class means you probably don't get a lot of free time." Crookshanks jumped in her lap to avoid a hyperactive cat that had been following him.

"Why aren't you following his example then?" Harry wondered. "You could beat him easily if you tried."

"Because I like to enjoy my free time. Who else is going to make all of those clothes for the elves?" Hermione lifted Crookshanks into her arms and held him like a mother would a child.

"Maybe he is trying to make a cook book," Ron suggested jokingly.

"What makes you say that?" Harry laughed. One of the cats tried to jump into Professor Binn's lap but screeched and ran off when it fell through him.

"I don't know. He's Mr. Perfect. Maybe he needs a secret hobby that doesn't include school work," Ron shrugged.

"You're just saying that because you are hungry," Hermione rolled her eyes.

"So? I bet he makes some damn good cupcakes. I wouldn't mind trying some." Ron grinned at Hermione's exasperated look. "Come on, what does it even matter? It's his loss. I'm having a grand old time."

"Yeah, but today is one of the few days we can have fun together despite being horrid house rivals. As one of the most influential students in the school, shouldn't he be participating?" Harry questioned.

"I don't think it matters," Ron pointed to a Slytherin student helping a Gryffindor up off the floor. "They seem to be doing fine without his almighty influence."

"Mr. Riddle, you are up next," The monotone voice of Professor Binns announced.

Harry watched as Tom calmly put his book in his bag and walked up to the front of the classroom. He held his head high and payed no attention to the chaos of the room. Cats were standing on desks and one was attacking a Slytherin scarf in the middle of the floor.

The room quickly fell silent as he took the podium. Harry was curious as to what he would talk about. He didn't expect perfect Tom to follow along with their little game, and would probably talk about something serious. He was proved right when he started talking about World War II.

"While we can create spells to harm and kill other humans, we have never created anything as devastating as the Muggle atomic bomb. The first bomb they dropped immediately killed 80,000 people and as the days would pass it would continue to kill tens of thousands more. But they did not stop there. They would go on to drop another bomb that killed an estimated 40,000 people." Tom lectured.

The previous happiness that had been in the room had been wiped away, replaced with a feeling of horror. Tom had accompanied his speech with photographs of mushroom clouds, victims of radiation, and the dead piled up in the streets.

"The war killed and estimated seventy-two million people on both sides. What wizarding war has ever reached that amount death? People who did not even wish to fight, where forced to flee their homes or worse. They even made camps that served no other purpose than to kill people they did not ally themselves with by the masses."

They listened as Tom continued to go into gruesome detail about the war and when he finished, he returned to his desk like he had not just traumatized the classroom. No one was able to get another laugh out of their presentation. When the next student tried, she received nothing but blank stares and an awkward cough.

Harry became infuriated as he watched Tom's attention turn back to his little book, not even bothered by the uncomfortable air in the room. "Who the hell does he think he is," Harry whispered to his friends.

"I thought it was good. Gruesome, but good." Hermione replied. "He doesn't have to make it funny. It's not a written rule anywhere."

"Yeah, but he can't just ruin everyone's fun just so he can have a good grade. He knew what he was doing." Harry argued.

"Mate, just let it go." Ron told him. "Sure that was messed up, but you're making this bigger than it is." Harry didn't respond but spent the rest of the class glaring at Tom.

When the presentations were thankfully over, the cats rushed out of the classroom as soon as the doors were opened. Harry, Ron, and Hermione followed the herd of animals and made their way down to the great hall for lunch.

Ron started talking to Hermione about the presentations, but Harry wasn't paying attention. His eyes were still fixed on Tom Riddle, glaring as he walked in the hall with his friends by his side, his book was clutched tightly in his hands.

"What do you think?" Hermione asked Harry who was watching Tom laugh at something one of his friends said. "Harry?"

"What? Sorry, what did you say?" His attention snapped to her.

"Honestly… What do you think Professor Binns thinks of all the pranks the class pulls for this project? I mean as many years his students have been doing this you think he might have learned something from it by now. I mean if we are all desperate for a good laugh, you think he would know to change his teaching method." Hermione explained.

"Aren't ghosts unable to change because they're you know… dead? Maybe he was really this boring when he was alive so now he is stuck like that. Like how Nearly Headless Nick didn't get his head chopped off all of the way and now he is out of the headless club for the rest of eternity." Ron suggested.

"Sounds reasonable enough. Does that mean, if you get stuck wearing one of your mum's sweaters then that's all you'll be able to wear for the rest of your ghostly existence," Harry teased.

"Hey, that's my mum you're talking about. I would be proud to show off a famous Weasley sweater forever. Show the rest of these ungrateful kids what real fashion is," Ron said with pride.

They made their way to the Great Hall and sat down together for dinner. As usual, it was filled with students chatting about the latest gossip and who they thought would win the next quidditch match. For some reason, Harry still couldn't get the irritating thought of Riddle out of his head.

He looked over to the Slytherin table and once again, Riddle was ignoring the excitement around him in favor of his book. It made Harry's blood boil and he couldn't figure out why. There was nothing wrong with wanting to get in some extra studying in for exams, or even doing something fun for a hobby. Harry just thought that hanging out with your friends and paying attention to them every once in a while was important too.

What kind of life was Riddle leading if he didn't stop to enjoy it every once in a while? The thought made him more than curious. Somehow, he knew the answer would be in whatever Riddle kept writing down.

* * *

"This is a stupid idea," Harry told himself. When he got obsessed with something, Harry usually went all out. Once during his first year, He thought that Filch had been keeping a three-headed dog somewhere in the school all due to the fact that Harry had seen him acting sneaky during school hours and followed him to an abandoned classroom only to hear loud parking noises coming from the inside. It turned out that Filch had only been trying to learn how to cast magic as a squib and had been shouting in frustration when he couldn't do it.

Not all of his obsessions had turned out as failures however. Another year, he had some suspicions about the new defense against the dark arts teachers. "No one wears that much pink and is that horrible of a teacher unless they have something to hide." It started off as a joke, but it turned out that his now former professor had been trying to trick students into casting dark magic as a ploy to get Dumbledore fired from his job. As soon as Harry found out, he had written to his parents who had started investigating immediately. It still brought laughter to his eyes when he remembered her being dragged off by the Aurors.

His new obsession was Tom Riddle.

Harry had watched him for weeks now. Even going so far as to staying behind during Christmas break to keep an eye on him. Even while they celebrated Christmas dinner in the great hall, Riddle did not pay attention to anyone around him in favor of his book. He had also caught him several times in the library reading books from the restricted section and quickly writing down his findings.

Every time Harry tried to see what books Riddle was reading, they would either be too far away to read or he would have put them away so quickly that Harry didn't have a chance to get a good look at them.

He didn't understand what was so important in his black book that he couldn't spend more time socializing with his friends. Every time Harry saw him, he had the thing in his hand. It only drove Harry's curiosity into finding out what he wrote in it all of the time.

The invisibility cloak was the only reason he had not been caught. He had tripped over a suit of armor twice now because it was so dark, and it was almost impossible to see with a new moon out. There was almost no light coming in through the windows because of it. Harry had memorized Tom's prefect rounds so that he would not run into him, and with some clever bribing to a first year Slytherin, he obtained the password to the common room.

It was late enough that when he walked into their common room, most of the students were asleep in their beds, and those who were still awake were dosing off in their chairs. All Harry had to do now was figure out which door led to the sixth-year boy's dorm.

Harry's good luck seemed to be paying off again, because he was able to follow another boy whom he knew to be in his year, down a flight of stairs and into the room where he needed to be. There were beds in a circle much like the Gryffindor dorm, except this room looked to be more spacious because the celling was made of glass and Harry could see up into the black lake. He had to take a moment to admire the beauty of it.

From his window in his dorm, Harry could see onto the school grounds and imagine himself flying whenever he wanted. Looking up into the lake, Harry felt both like he was trapped beneath the water and as though he could swim up and be wherever he wanted to be. It was a strange combination of feelings and he didn't want to experience it longer than he had to.

He found Tom's bed easily enough, his initials were on his trunk and his area looked to be as clean and perfect as he usually dressed. The rest of the beds looked untidy and some looked to not have been cleaned in several weeks.

Harry moved as quietly as he possibly could so he wouldn't get caught. Strangely, Harry found Tom's black book with ease. It was left under his pillow without any sort of concealment charms. The black leather book looked completely harmless. Why the hell would he just leave it here? If this damn this is so important to him, isn't he worried that someone like me would come snooping around?" Harry thought to himself.

His question was answered as soon as he opened the book. "What the hell?" He cursed quietly. Every page was written in a strange and squiggly lettering that Harry was sure that only Tom Riddle would be able to understand. Harry waved his wand over it to see if it was merely a concealment charm meant to confuse him, but nothing changed. He wanted to throw the thing across the room in frustration at his lack of answers. Instead, he carefully placed the book back under Tom's pillow and left the room as quickly as he could.

No answers and now he was turning into a creepy stalker. Harry didn't feel proud of himself at all, but he still didn't want to give up.

On his way back to his dorm, Harry ended up tripping once again on a suit of armor, except this time, he knocked the whole thing over creating a loud noise that woke up all of the paintings around him.

"What in the blazes is going on!" A portrait of a man wearing a long bright orange robe exclaimed. "Don't you know what time it is! Quit making all of that noise! Some of us are trying to get some sleep!"

A bright light appeared temporarily blinding Harry from his spot on the floor. "Yes, what exactly are you doing Potter?" A familiar voice spoke. Harry turned to look just who had conjured the light and felt his blood run cold. Tom Riddle stood above him with his arms crossed and an unamused look on his face. "You do know that it is after hours, right?" Tom asked.

"Yes," Harry said through his teeth as he got to his feet and brushed himself off.

"Is that an invisibility cloak?" Tom said while gesturing to the silvery fabric in Harry's hands. "You realize those don't work if you go around making an obnoxious amount of noise, right? You need to be silent to stay completely unnoticed."

"Yes, I know that," Harry replied irritated.

Tom looked unimpressed with Harry's response. "I'll ask again, what are you doing out here? You should be in your dorm like everyone else."

"I was taking a late-night stroll. Helps clear the head. Maybe you should try it sometime," Harry lied.

"Of course," Tom rolled his eyes. "How about you tell me what you were really doing and we can avoid the drama."

Harry considered his options. He could spend days, even weeks trying to figure out what language Tom's writing was in, or he could be honest and just ask.

Harry's boldness took over. "I snuck into the Slytherin dorms."

"You what?" Tom said surprised, clearly not expecting that answer.

"You heard me. I got curious about you so I snuck in." Harry tossed the invisibility cloak over his shoulder, clearly having no more need of it.

"About me? You're not one of those murderer stalkers, are you? I don't have time for things like that." Tom looked annoyed at the idea.

"No of course not. Well…yes. Temporarily stalking. Not anymore though," Harry shrugged. "I had to know. You had such potential to help in the fragile unity between our houses but all you did was write in your little book and talk about World War II."

"You don't think World War II was important?" Tom challenged.

"I think it is important. But spending time with your friends and having a good laugh is important too. All I ever see you do is ignore them and write in your book, which is impossible to read by the way. Ron thought you were making a secret recipe book for cupcakes or something. What language is that in anyway, and what the hell is so important that you would ignore them. Are they that boring to you?" Harry ranted. "You shouldn't spend all of your time studying or doing whatever it is you are doing or you'll miss the important things."

"Like what," Tom looked at Harry with genuine interest. "Not that I'm dropping the fact that you snuck in to my dorm to read my diary, but let's continue with whatever it is you are talking about."

"You're…uh." Harry awkwardly scratched the back of his head. "Listen, I just don't think it's healthy for anyone to spend so much time working. You need to live a little. Go outside and enjoy a quidditch game, no wait you don't like quidditch. Go… I don't know, go do something."

Tom's eyes seemed to be showing an emotion that Harry didn't quite understand. "Are you worried about me, Harry?" Tom took a step forward. "What would you suggest would help me _live a little?_ You must have an idea better than quidditch."

"Uh…" Harry didn't know how to answer Tom was getting closer to him and Harry couldn't figure out why.

"Come on, Golden Boy Harry Potter must have some clever ideas. Surrounded by his friends all the time, idol to the Gryffindor image… I wonder what you get up to sometimes. You do have a legacy to keep up don't you? I've heard about what your father and his friends got up to in their time." Tom smirked. He was now only a few inches away from Harry's face who still didn't understand what was going on. "And you are worrying about little me? I'm touched."

"Yes, well," Harry said while backing up against the wall. "It didn't look like your friends were very worried about you. Sorry, I tend to get a little obsessive sometimes. I'll stop. Promise."

"Do you? What if I don't want you to. Maybe you are right. I do need to learn to live a little. That is the goal after all…" Tom grabbed Harry's face and closed the last distance between them.

Completely unexpecting the kiss, Harry didn't react at first. His hands were by his side as Tom's hands continued to grip his face and his lips moved against his. Only after the initial shock did Harry close his eyes and press his lips back against Toms.

He didn't completely understand what was happening or why it was happening, but he found that he didn't mind either way. Tom pulled away too soon for Harry and it took him a moment for him to open his eyes again.

"I wasn't… I didn't mean _that,_ I just… uh…" Harry was at a loss for words.

"You didn't like it? Have I miss understood your intentions?" Tom looked at Harry in confusion.

"No, no," Harry started. "Well, yes. Sort of. I didn't mean to… live a little with me, but...I can't say that wasn't an experience."

"Oh." Tom looked surprised. "I thought that you were stalking me for other reasons. I obviously misjudged the situation." Tom suddenly became cold to Harry. His previous playful attitude was gone.

"No, I didn't mean. Yes, I didn't mean it that way initially, but I'm not against you and me, oh how do I say this?" Harry looked like he was thinking for a moment and then smiled at Tom and said "Do you want to go to Hogsmeade on the next trip? I wouldn't mind going with you if you were interested. It's on new year's eve and I think they are lighting fireworks before everyone has to be back at the school."

Tom seemed to contemplate the idea for a moment before responding "Okay, but if you are just pulling some kind of prank on me, you won't live to regret it."

Harry couldn't tell if Tom was joking or not. "Right, well I need to get back to Gryffindor Tower so, I'll see you then?"

"Don't be ridiculous. You'll just knock something over again. I'll walk you there." Without looking back at Harry, Tom started walking in the direction of Gryffindor Tower.

"How do you even know where it is?" Harry asked as he fell in step beside him.

"I'm a Prefect Potter. They tell me a lot of things." Tom rolled his eyes. "Also, you Gryffindor's aren't exactly good at keeping its location a secret. How did you get into the Slytherin common room?"

"I bribed a first year," Harry replied proudly.

Tom snorted. "Clever."

* * *

Harry didn't know how to react to Tom the next day. He saw him walking on the opposite side of the hall with his friend and Harry froze. When Tom locked eyes with him, he smiled and waved like it was a normal thing. Harry could only smile and wave back to him.

At lunch, Harry pulled his courage and sat down with him at the Slytherin table. Those still left at the school during break looked at them in confusion and curiosity, others in open shock. Harry put a sandwich on his plate, and poured himself a glass of pumpkin juice like it was the most normal thing in the world.

"You don't have to put that much effort into this you know. I'm sure you would be more comfortable sitting over at your own table." Tom said while he was writing in his diary.

"Yeah, but if I get to know you a little now, then Hogsmeade will be more fun," Harry replied before taking a bite of his sandwich.

Tom shook his head. "If you insist."

Harry finished his bite and looked at Tom's dairy. He still couldn't understand what it said. "What do you write about in there anyway? Couldn't you just use charms to ward off other people?" He asked.

Tom looked at Harry with a raised eyebrow and said "It's private, and anyone can dismantle a ward if they try hard enough. But, maybe I'll tell you one day, that is if you show me how to 'live a little'."

Harry laughed. "Okay, you're on."

They spent the rest of their meal talking and enjoying each other's company. Harry found out that Tom had the best sense of humor. He laughed at the things he said and enjoyed his comments on the stories he told.

Harry had a better time than he thought he would with Tom. He had been nervous at first, but he was surprised at how quickly he relaxed. They had ended up spending every meal together until the day of the Hogsmeade trip arrived.

Together, they walked down into the snowy village. Their first stop was the bookstore at Tom's insistence. To Harry's surprise, Tom walked over to the muggle section first thing.

"I thought you didn't like muggles," Harry wondered.

"I don't, but it wouldn't be very smart of me to be ignorant about them. Didn't you hear my presentation, or did you fall asleep." Tom said while he was searching through the titles.

"No, I was listening. Who wasn't?" Harry shrugged.

"What did you think then," Tom asked genuinely curious.

"Well…" Harry was afraid to answer honestly, but he didn't want to disappoint Tom. "I thought that it was interesting but you focused on all of the negative aspects of their culture. Yes, World War II was horrendous, but muggles have come up with amazing things too."

"I have no doubt that they have, but with all of our power we choose to hide away from them. We used to be hunted down because they didn't like us. If they knew we existed now, and they still don't like us, how fast will they turn their weapons against our kind? I don't know of any spells that can protect against an atomic bomb, do you?" Tom explained.

"Me neither, but what if they do like us? What if they've changed. I don't see a point in hating a whole culture for something they _might_ do," Harry argued.

"I'm not willing to take that risk," Tom told him seriously. "But enough about that. Here." Tom pulled a book from the shelf and handed it to Harry. "Muggles do invent some pretty interesting things. I thought you might like this."

Harry looked at the book in his hands and busted out laughing. It was a muggle recipe book for desserts. "Are you trying to get me to cook for you?" Harry opened the book and turned to a random page. It showed a picture of carefully decorated pumpkin cupcakes.

"No, but you can pretend that really am writing a cook book. I'm sure it will give your friend a good laugh. I like magical sweets, but there is something special about the way muggles make theirs that magic smiley can't replicate." Tom admitted. "You can cook something for me out of there and I might forget the whole stalking thing."

"Okay, but no promises on how well it will taste. I'm not much of a cook," Harry laughed.

They spent the rest of their date wandering around Hogsmeade and chatting about everything that crossed their minds.

Finally, it was about time for them to be heading back. They were on the path back to the school, the town growing smaller in the distance, when the sounds of loud bangs could be heard from behind them. The fireworks lit up the sky in all shapes and colors. Harry looked up to them in wonder, but Tom seemed unimpressed.

"Here," Harry said while taking a package out of his pocket. "Happy birthday."

Tom looked at Harry with suspicion but opened the package. He smiled when he saw what it was. "Another diary," he noted. "It's the same as the one I have."

"Turn it over," Harry encouraged.

Tom's eyebrows raised when he saw a small golden inscription of his fill name on the corner.

"I know you like your secrets, and I won't pry about your other diary anymore. I hope you like it." Harry smiled.

"Thank you," Tom said sincerely, holding the new diary to his chest. "I mean it. Thank you."


	2. Chapter 2

_**December 17**_ _ **th**_

 _I thought about joining in everyone else in their little game, some of these presentations are clever at best, but I couldn't miss this opportunity to show these people the true nature of muggles. I'm honestly not happy to ruin all the fun, but they need to know. Otherwise, most of these people will spend the rest of their lives ignorant to the true savage ways of the muggles. I hope I get through to at least some of them._

 _Potter keeps staring at me. What the hell is his problem?_

 _ **December 20**_ _ **th**_

 _I've noticed Potter starting at me more and more recently. Either I have found another follower to my cause, or he is like those other annoying girls who has a crush on me. Both can be used to my advantage if I play my cards right. I really need to get into the restricted section again, there might be another spell to strengthen the protection of my future horcruxes._

 _ **December 25**_ _ **th**_

 _With most everyone gone for the holidays, I thought I would be able to spend more time on my more personal projects, but I keep feeling someone's eyes on me. I don't know who is following me but I am sure as hell going to find out._

 _I wish Potter would either act soon, or stop staring at me. He is really getting on my nerves._

 _ **December 27**_ _ **th**_

 _I was making my rounds and I found Potter. It turns out, his stalking was more serious than I thought. He was determined to find out what it was that I was writing in here, not that it is any of his business. He even managed to sneak into my dorm and get his hands on it without anyone finding out. Well, no one would have but he actually admitted it to me._

 _I thought about cursing him right there and then, but his reasons actually gave me an idea. If Potter noticed that I was acting strange, how long with it be until someone else comes poking inside here?_

 _He told me some shite about house unity, and how I should be spending more time with my friends. But, there was one thing that really stuck with me. He told me he wanted me to "live a little"._

 _I'll admit that my focus on my horcruxes has made me withdrawn to the world, but it is a price I will play if it means my immortality. However, that doesn't mean I can't fool around every once in a while._

 _I kissed him, which seemed to surprise him._

 _I knew that he didn't mean he wanted me to "live a little" with him, but I wasn't going to pass up the opportunity to mess with him. He did try to read my dairy after all._

 _It worked far better than I expected. He wants to go to Hogsmeade with me on my birthday, not that he knows it's my birthday. Still, it will be better than spending another year hunched over a desk._

 _The best part is it will prevent other people from thinking that I am up to something. Dumbledore cannot be avoided, he always thinks that. But, everyone else should be happy seeing me socializing with my peers._

 _ **December 29**_ _ **th**_

 _I am disappointed to say, that I enjoy Harry Potter's company._

 _ **December 31**_ _ **st**_

 _I'm confused._

 _Harry has been interesting to hang out with. He doesn't agree with everything I say, but he is always open to listen to me. It is nice to have someone to discuss my beliefs with without instantly shutting me down simply because I am a Slytherin._

 _We spent the afternoon in Hogsmeade and to my surprise, he got me a birthday present. I have no idea where he found out my birthday, but I suppose stalking me for so long, he had to have learned something._

 _I don't think I ever appreciated the fireworks before either. Maybe "living a little" won't be so bad after all._

 _ **January 20**_ _ **th**_

 _Harry and I have been spending too much time together. I am starting to get attached and I do not like it. I found myself missing his company last night and now I am anxious to see him this morning._

 _This needs to stop, but I can't get his "live a little" phrase out of my head. I hope this passes soon, I have plans I need to get started and I can't do it with him constantly in my head._

 _ **February 10**_ _ **th**_

 _Dumbledore has crossed the line._

 _He thinks that I am just using Harry for my own personal needs and… I don't know if he is right or not. It started out that way, but now…_

 _I hope I can convince Harry to join me. The future I have planned will be so much more if_

 _I can't wait any longer. He will be the fuel for my first Horcrux, and I know just how I will do it. The basilisk would love to eat the muggle loving fool for me._

 _ **February 11**_ _ **th**_

 _He's dead._

 _ **February 15**_ _ **th**_

 _I met his parents. Mrs. Potter said that Harry had written a lot about me in his letters. I don't usually like physical contact, but I did not turn away the hug she gave me. I do not know who needed it more._

 _He was not the kill I wanted, but I will not let his death be in vain._

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 _ **Unknown**_

 _Hello, my name is Tom Riddle. How did you come by my diary?_


End file.
